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Fate of the Oxygen Atoms in the Diol‐Dehydratase‐Catalyzed Dehydration of meso ‐Butane‐2,3‐diol
Author(s) -
Speranza Giovanna,
Morelli Carlo F.,
Orlandi Maximilian,
Scarpellini Mauro,
Manitto Paolo
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010228)84:2<335::aid-hlca335>3.0.co;2-k
Subject(s) - chemistry , diol , butane , catalysis , propane , substrate (aquarium) , medicinal chemistry , stereochemistry , organic chemistry , oceanography , geology
18 O‐Substituted propane‐1,2‐diols and meso ‐butane‐1,2‐diols were synthesized and fed to growing cells of Lactobacillus brevis . Propan‐1‐ol and butan‐2‐ol, prepared from such diols through diol‐dehydratase‐catalyzed dehydration followed by intracellular reduction, were analyzed for their 18 O‐content. For each propane‐1,2‐diol enantiomer, partial retention or complete loss of the isotope appeared to be related to the mode of substrate binding. Specific retention of the O‐atom linked to the ( R )‐configured C‐atom of meso ‐butane‐1,2‐diol indicates that the diol dehydratase handles this substrate like ( R )‐propane‐1,2‐diol.